Potassium Carbonate → 2-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 661884

반응식

HRID 661884 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[C:10]1(=[O:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(Cl)Cl.[Cu]I>[Br:8][C:4]1[C:3]([CH3:9])=[C:2]([N:11]2[CH2:12][CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:20])[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 346812,6-Dibromotoluene2회HCID 1508963,4-dihydroisoquinolin-1(2H)-one2회

생성물 1

HCID 593751142-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one수율 66.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

Step 2 A mixture of 1,3-dibromo-2-methylbenzene (340 mg, 1.359 mmol), 3,4-dihydroisoquinolin-1(2H)-one (100 mg, 0.679 mmol) and potassium carbonate (94 mg, 0.679 mmol) in DMSO (2 mL) was purged with nitrogen, treated with copper (I) iodide (25.9 mg, 0.136 mmol) and heated at 150° C. for 3.5 h. The mixture was combined with that from a second reaction using 1,3-dibromo-2-methylbenzene (2.59 g, 10.36 mmol) and 3,4-dihydroisoquinolin-1(2H)-one (508 mg, 3.45 mmol), diluted with DCM and filtered through Celite. The filtrate was washed with 5% aqueous ammonium hydroxide, dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc) to provide 2-(3-bromo-2-methylphenyl)-3,4-dihydroisoquinolin-1(2H)-one as a yellow solid (142 mg, 11%). 1H NMR (400 MHz, chloroform-d) δ 8.15 (1H, dd, J=7.70, 1.10 Hz), 7.55 (1H, dd, J=7.92, 1.10 Hz), 7.46-7.51 (1H, m), 7.37-7.42 (1H, m), 7.24-7.28 (1H, m), 7.17-7.21 (1H, m), 7.09-7.16 (1H, m), 3.95 (1H, ddd, J=12.21, 10.12, 4.73 Hz), 3.73 (1 H, ddd, J=11.94, 6.33, 5.28 Hz), 3.26 (1H, ddd, J=15.74, 10.23, 5.28 Hz), 3.06-3.14 (1H, m), 2.36 (3H, s). Mass spectrum m/z 316, 318 (M+H)+.

후처리

  1. customwas purged with nitrogen
  2. customfrom a second reaction
  3. filtrationfiltered through Celite
  4. washThe filtrate was washed with 5% aqueous ammonium hydroxide
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (eluting with hexane-EtOAc)

출처 및 근거

ORD 기록
ord-98e0e8da894c45a68096c12098af0b37
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

연결된 노트

불러오는 중…